Hi Mitch, my wife and I just went through the same scenario you are talking about and I just wanted to say it’s doable. I would just say that the only difference is it sounds like you have more experience than we did.
I have owned a whitewater kayak and a Hobie Cat, that was the extent of my boating knowledge. My Dad was in the Merchant Marines all his life and he would take me aboard when they would come into Norfolk and I would Ride down to Southport with him on the cargo ship. Guess that’s why I have a little salt in my veins.
About a year ago as I was pondering retirement we were trying to come up with an adventure plan for while we were still in good enough health to tackle. I always had rose colored glasses about living on a boat and traveling. I started planting the seeds with my wife by watching on the YouTube channel shows such as: Searching for C-Shells, Sailing Zatara, Gone with the Wynns. I followed that up with our first cruise after Christmas before Covid hit. To my surprise my wife went along and thought it would be a fun adventure for retirement. I spent the next 6 months researching all kinds of boats, developing a budget we could afford, and reading everything I could find on the internet. Long story short we sold our home, downsized to a 12 x 14 storage unit, bought a boat, moved from a Idaho to San Diego to live on it full time as of July 27, 2020.
We bought a 1985 Kadey Krogen 42 ft which is the perfect size for our goals . There Are a lot of things I would have done different if I had knew then what I know now. But if you wait and wait for all the stars to align, you probably will have waited to Long.
We are in San Diego for next couple months. Send me a private message if you want to talk more or come down to see Amelia (KK 42) to get some idea of hoops you will need to jump through. Good luck. - Barry